Helping Jess Pt. 05

"You might be surprised, but this whore is actually a very high powered executive. She had her own business worth millions that was bought by a big multinational and she now works as country manager for that multinational company, and manages over 100 people. Her trouble is that she craves humiliation and someone else to control her and force her to admit to her basest needs and act like the whore she is." Her whore seemed to blush at this, but I couldn't be sure.

Jess wants to show me something, so I'll leave you with my whore – I understand that you wanted to sign the terms and conditions for the study, I'll let the bitch show it to you.

Claire and Jess left the room. Holly came in front of me and took out a pair of handcuffs. She attached this to my left hand, then the other part to the hook of the chastity belt. I was effectively one handed.

I tried to apologize for the earlier gagging I had forced on her. She didn't seem to be listening. Eventually she came round in front of me and slapped me hard in the face.

"You fucking wanker, thinking you are a tough man, you hurt me, my throat feels bruised. These tears and real and you just kept on and on going and hurting me again and again. No doubt enjoying being a bullying horrible man."

I was horrified, this was everything I didn't want to be, a bully victimizing women, an aggressive man, a sadist in all the wrong ways. "I am so sorry, I don't know I got carried away, please let me make it up to you."

"I will take my revenge on you in my own time, and you will regret being such a bastard, when clearly you are just a wimp. For now, you need to read and sign this agreement. Be quick about it as Master has said I can have an orgasm tonight if I do everything right and we get back on time."

She put the agreement on the table and went and sat on the sofa. She looked gorgeous still – naked except for her chastity belt and those long red boots, her breasts small and pert. I started wondering how long it had been since her last orgasm.

She saw me looking at her, then walked over to me, and without saying anything gave me another big slap in the face. It hurt!

"I told you to read and sign the agreement, not gape at me you stupid bitch. I can see why Master thinks you are such a stupid fucking sissy."

Geez, and I thought things couldn't get worse, but now Claire's whore was slapping me around. I could see I was the bottom of the pile. I quickly started trying to look at the agreement. It was hard though as I could hardly raise my head above the level of the table. I could lift up the agreement a bit, though it was 3 pieces of paper stapled together, and difficult to maneuver one handed.

I could see odd words and phrases on the first piece of paper which seemed pretty straight forward:

- University of Dolchester

- 2 weeks of chastity

- Key to be held by Claire Coombes

- No physical harm to come to subject

There was also a lot of legal types of words making it hard to read. It was particularly hard to read the second and third page having only one hand and the pages were stapled together. It looked ok though so I said so.

"Well sign the fucking agreement then you stupid bitch," was the response I got.

I reached up and took the pen that was next to it, and strained and signed at the bottom.

After I had done that, the whore squatted down in front of me.

"So sissy, your life will be difficult from now, Master already knows you are a stupid male thinking of all the wrong things, and after you hurt me earlier, I promise to get revenge."

"Please, I am so sorry for what I did earlier, I got carried away and certainly didn't want to hurt you."

"The fact is you did hurt me and you knew it could be hard. These are just words and you are just saying that to try and reduce your punishment bitch."

I thought it better to say nothing and not make things worse. My legs were beginning to ache in this squatting position, they would cramp soon, I would probably need to sit down soon.

"Oh sissy bitch, you need to sign all the copies, there are 2 copies. Then I can release you."

Release sounded good, so as she lifted up the papers so I could sign the later sheets, I signed at the bottom of the 2nd and 3rd pages.

The whore seemed quite happy at this and gave me a kiss on the lips. "thank you, now I hope I can get my orgasm. It has been 3 weeks and it has been hard."

She proceeded to unlock the handcuffs first, then the lock on the chain attached to the trapdoor lock. I stood up relieved, I felt that I would have cramped before long, unless I had sat on the floor.

She left the room and shortly Claire and Jess came back in. Both Claire and Jess looked quite happy. Claire spoke to me.

"So Belle, I understand your worm has a pretty name – Phoebe is it?"

I nodded at that, not trusting myself to speak.

"That's very pretty, I like that. Whenever we meet, I would like you to pretty up Phoebe – put some pretty rings or jewelry on her. I am sure you can ask in a shop what would be best."

She laughed at that. I was shocked – this was my manhood, and she was totally emasculating me.

"Anyway Belle, Jess and I have been making some plans. You will both come over on Sunday. You will spend Sunday being a maid.

I understand you go out Friday night, and Saturday Holly has another engagement.

Your current dress is cute, but not nearly effeminate and girly enough for a sissy like you. I have a better one that Holly will bring over on Thursday evening. Holly will sleep here thursday night. You will take a day off on Friday and you and Holly will spend time practising making you as effeminate as possible."

"On Sunday morning, Holly will come over early and you will get you ready into your new uniform. You will get up at 7am and spend 3 hours getting you ready. If I cannot see significant improvement from today, you will both be punished."

"The three of you will then come over to mine. Holly is allowed to wear one piece of clothes of her choice, she'll probably choose the coat as always . She will have to wear lingerie of my choice. It will be very slutty – she will be in service Sunday evening. Your mistress will put on one of her best cocktail dresses, she will be the lady of the house Sunday afternoon and must look respectable, elegant and beautiful before she gets the humiliation she deserves. Jess, no underwear, I will give you something slutty, but it won't stay on you for long, you will get into the role of a fucktoy quickly. Your role will likely continue into Monday.

Belle, you little sissy eunuch are to wear your new maid's uniform and not one single piece of male clothing is to travel with you. You will be in another town as a maid, without a stitch of male clothing in another woman's house and completely exposed if you misbehave. I will kick you out if you piss me off. Your mistress will be unable to help you, so I suggest you try very hard to keep in my and Holly's good books. Do you understand?"

"Yes Madam," I said quietly.

"Madam? I like the improvement in respect, but Master is better. I want you to suck my cocks a lot, I will buy many for you. So call me master going forward. And don't worry I won't force you into any bi experience, I understand that is a limit. However I will ask every woman there to use a strapon with you, you will become an expert on giving strapon blow jobs, and getting pegged."

These were statements, not questions. I looked at Jess, she seemed quite happy with all of this. I was not so sure.

"In the evening, your mistress will stay at mine for a night of debauchery according to my menu. You will go and spend the evening with Holly here."

This sounded bad, my new beautiful enemy. Holly looked quite happy, I kept quiet.

"We are not yet sure what will happen Monday, we'll find something."

Holly spoke up.

"Master, please may I suggest something?"

"Yes Holly?"

"May I make suggest master that on Monday, we spend a lot of time making this sissy pretty and playing dress-up games and modelling several dresses I have. Then also my place is a bit messy, can she practice being a maid there?"

"Yes, that sounds good. She needs the practice. Let's agree that. I assume you have no objection Jess?"

Jess simply shook her head. I wasn't asked my opinion.

Claire continued, "OK, we have to go, but before we go, one last present for you Belle."

She gave me a package that I unwrapped, inside were waxing strips.

"Thank you master, very nice."

"Use them well sissy, you are not allowed to have any hair below the neck. The exception is the genital area where Jess and I need to talk, and we'll let you know our decision. By Thursday night, make sure you have used these strips. If you fail, we will do slow waxing on you, which is torture. On the other hand I think you will enjoy the sensation on your legs once you put nylons on.

"Now before we leave, I need to change the locks, the previous one could be broken into too easily, so come closer, pull down your panties and hold up your dress."

I did as I was told and she took off the previous lock. Then she pulled out a new lock from her handbag, it was HUGE, more like one of those you put on steel industrial doors.

She saw the look on my face, so did Hailey who laughed, Jess also had a big smile on her face.

"Yes Belle it is big, this will be almost impossible to cut, but even more pleasing, it will be heavy and be another reminder of your predicament. There is no way you can forget this."

She clicked the lock together, it made a big click. When she let go, it was heavy, very heavy, dragging my tackle down.

I was in shock thinking how could I walk with this heavy weight around my balls. I was probably going to need to wear extra underpants, well – panties now. There was a pause, as if they were waiting for something, Jess spoke up "Belle, you are forgetting to smile and say thank you. I will punish you later for both."

This was like a face slap. I tried to apologize and look happy – hard to achieve with my thoughts, and I think that I wasn't fooling anyone. Hailey looked very amused with my discomfort. I saw them out and returned to face Jess.